4-AcNH-TEMPO-CATALYZED OXIDATION OF ALDOSES TO ALDARIC ACIDS USING CHLORINE OR BROMINE AS TERMINAL OXIDANTS

Abstract

The 4-AcNH-TEMPO-catalyzed oxidation of d-glucose to d-glucaric acid using elemental chlorine or bromine as the terminal oxidant is reported. The pH and temperature of the reactions were closely controlled to be between 0–5°C and pH 11.5, respectively. Spectroscopically (¹H NMR) determined yields of glucarate were greater than 90%; yields of crystalline monopotassium d-glucarate (or disodium d-glucarate), isolated and purified by precipitation, were between 70 and 85%. Oxidations of mannose to mannaric acid and galactose to mucic acid were also demonstrated.

ACKNOWLEDGMENTS

We would like to thank Ruben Mamani-Paco, University of Connecticut Department of Chemical Engineering, for technical assistance in the setup of the oxidation reactor and Charles Gallo, University of Connecticut Technical Services, for designing and building the pH control interface. CB would like to thank the UConn Research Foundation for financial support.